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Sending, receiving, and organizing email in Outlook.com
Outlook emails not working
James Earls Thompson
0
Reputation points
I gave permissions to Google to share my account with Microsoft in January 2026, and we were getting our emails in a timely manner, however, for some reason, Outlook is not sending all our emails now. The last one was in February. We have the Microsoft 365 Family Plan, and I tried to get some help because I am now 83 and, unfortunately, I am not good with maneuvering through technical instructions. It is totally impossible to speak to Microsoft support. Yesterday I tried to speak to someone and was placed on hold for an extended period of time, however, I was then directed to a game called, Beat the Robots, which I thought that I "had to" play in order to be connected, but having rheumatoid arthritis, I could never beat the speed of A.I. robots. 35 minutes wasted. Extremely annoying, frustrating, and very unkind for Microsoft not giving any thought to its elderly clientele, to say the very, very least.
Please help me. 😢
Move from Microsoft 365 and Office | Other
Outlook | Web | Outlook.com | Email
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Hornblower409 14,925 Reputation points2026-06-20T19:00:47.26+00:00 If you are still having problems, type "Not Solved" in the "Add Comment" box below and then click the [Add Comment] button. I will try to offer some suggestions on what you can do next.
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James Earls Thompson 0 Reputation points
2026-06-20T19:54:31.74+00:00 Please help me do whatever it takes to get our Outlook emails up to date. I already asked Copilot for help; however, often the instructions are immensely difficult for me to understand. I need a live Microsoft support person to contact me and resolve this regrettable situation.
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Hornblower409 14,925 Reputation points
2026-06-20T21:29:44.6066667+00:00 We have the Microsoft 365 Family Plan
Did you try this route? Is this were you ran into the Prove You Are A Human "game"?
- Go to the Microsoft Support contact page: https://support.microsoft.com/contactus/
- Sign in with the Microsoft account that has the Microsoft 365 Family subscription.
- In the search box, type “Chat with an agent” and press Enter.
- Select Contact support.
- Choose Products and services, then select Microsoft 365 & Office (or the closest option for subscriptions/billing).
- Follow the prompts until the option Chat with a support agent appears and select it.
- If preferred, choose Call me back instead of chat to speak with someone by phone.
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Hornblower409 14,925 Reputation points
2026-06-20T21:36:38.3766667+00:00 James said
I am now 83 ... having rheumatoid arthritis
Another possible option is the Microsoft Disability Answer Desk
https://www.microsoft.com/en-us/accessibility/disability-answer-desk -
Hornblower409 14,925 Reputation points
2026-06-20T21:56:47.0466667+00:00 James
Another option would be to have a trusted friend or relative use Windows Remote Assistance to connect to you PC and perform the steps suggested by Microsoft Support.
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